3-(N, N-diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2239-2242

  Al Sehemi, Abdullah G ^a   Atkinson, Robert S ^a   Fawcett, John ^a   Russell, David R ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; QUINAZOLINONE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034719803     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00138-6     Document Type: Article

References (11)

1. Atkinson, R. S.; Barker, E.; Edwards, P. J.; Thomson, G. A. J. Chem. Soc., Perkin Trans. 1 1996, 1047.
2. Atkinson, R. S.; Barker, E.; Sutcliffe, M. J. Chem. Commun. 1996, 1051.
3. We have previously shown that partial kinetic resolution of α-phenylethylamine with a DAQ was possible (Ref. 1).
4. cf. Atkinson, R. S.; Ayscough, A. P.; Gattrell, W. T.; Raynham, T. M. J. Chem. Soc., Perkin Trans. 1 1998, 2783.
5. Hunt, B. J.; Rigby, W. Chem. and Ind. 1967, 1868.
6. 2=0.1354 (all data).
7. The imide nitrogen of DAQ 4a is not exactly planar (Σ bond angle=353.3°).
8. For references to other twisted amides, see: Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577 and references cited therein.
9. By comparison, a competitive reaction of benzoyl chloride and isobutanoyl chloride for 2-methylpiperidine gave a 3:2 ratio of the corresponding amides, respectively.
10. The enantiopurity of the unreacted enantiomer was also determined by its reaction with (S)-α-acetoxylpropanoyl chloride: the de of the resulting amide was 89% as measured by NMR.
11. Craig, J.; Pindlar, A. R. J. Org. Chem. 1971, 32, 3649.